


Bet On It

by AlAngel



Category: Supernatural
Genre: Dean’s an asshole, F/M, fluff? I’m not sure, objectifying of women, stupid bets
Language: English
Status: Completed
Published: 2017-11-17
Updated: 2017-11-17
Packaged: 2019-02-03 16:52:52
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,797
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12752337
Author URL: https://archiveofourown.org/users/AlAngel/pseuds/AlAngel
Summary: When Dean notices the interest his new best buddy, the king of hell, has in the pretty bar tender, he proposes a bet to get under his friends skin. What happens however if Crowley is more sincere in his interest than he lets on in front of his friend?





	Bet On It

Title: Bet On It  
Character: Crowley x Reader, Dean  
Genre: fluff? I’m not sure  
Word Count: ~2.7k  
Warnings: Dean’s an asshole, objectifying of women, stupid bets,  
Summary: When Dean notices the interest his new best buddy, the king of hell, has in the pretty bar tender, he proposes a bet to get under his friends skin. What happens however if Crowley is more sincere in his interest than he lets on in front of his friend?  
A/N: Another story for my Khal Drogo anon. I know it has been months, but I didn’t forget about your Crowley story. Thank you for your patience. Enjoy.  
…

 

"Shush Dean. I'm watching" Crowley said his head turned towards the bar. An unobservant bystander would have assumed the boring man in the expensive suit was following the soccer match displayed on a small TV just above the bar. But Dean Winchester was anything but unobservant. He felt like he knew the demon king inside out after countless nights of partying together and enjoying whatever the day had to offer.  
"You could just go and talk to her" Dean suggested his eyes moving up and down the waitress appreciative "Tell you what I'll go talk to her for you."  
Now that made Crowley take his eyes off her to send Dean a warning flash of red eyes. The demon couldn't point anything specific down but he liked the way the woman moved and smiled. She was calm and relaxed even though he certainly wasn't the only one who more or less subtle admired the way her blouse hugged her curves in just the right places. For instance there was now also Dean looking at her with a slightly predatory grin, something that did not settle easy with Crowley's guts.  
He put a hand on his drinking companion’s arm, physically refraining him from going anywhere near her. The thought of Dean’s hand travelling over her body made him for some reason angry.  
"You will do no such thing"  
"Why wouldn't I?" Dean laughed and shrugged Crowley’s hand off "She's pretty, available and it's not like your about to make a move."  
"What if I were ‘to make a move’?"  
"Wouldn't make a difference" Dean grinned "I'm Dean fucking Winchester if I want a girl I can have her"  
"Modesty really isn't one of your strong suits, is it?"  
"Same as patience isn't yours" Dean smirked "Bitch"  
"Jerk"  
Once again Dean’s eyes travelled over to see her putting a beer in front of some customer who talked more to her cleavage while he thanked her. She did have something about her in the way her (y/e/c) eyes sparkle with amusement rather than annoyance at the behaviour. Self-confidence had always been something both Dean and Crowley found attractive in a woman.   
"Let's make a bet" Dean suddenly suggested his eyes never leaving her "Let the lady decide if she prefers some demon or a Winchester"  
"And who would win this bet of yours?"  
"Whoever gets her to sleep with him tonight" A cheeky grin spread on Dean's lips.  
"Tonight?" Crowley raised his eyebrows with amusement, he didn't like the idea of Dean touching the young bartender but the challenge of a bet intrigued him. "Aren't you a bit presumptuous?"  
"No" Dean emptied his beer and got up to get the refill at the bar, before leaving however he turned back towards Crowley "I'm just that good."  
…  
"Hello Darling" You turned as you heard the smooth voice of a new customer at the bar. The expensive suit was a bit out of place so it wasn't hard to recognize him as one of the men from a couple of the tables over. He was good looking and the sparkling gleam in his eyes was interesting. Usually you hated customers hitting on you, there were enough pretty girls around who gladly went home with a man who brought them a cheap drink first, so you hated to be the target of unnecessary and obnoxious flirtation. However this guy wasn’t the usual drunk halfwit that tried to get lucky with you and although he had a small tumbler with something from the higher up shelf in hand, he didn't seem drunk or tipsy.  
"Hey there yourself"  
"How’s your night?" He smiled at you which caused small lines to form next to his curled up lips. There was obvious interest in his eyes though you doubted it was actually for your night so far. Yes he was slightly different from the men that usual approached you, but at the end of the day most of them were the same when they saw a pretty girl in a bar.  
"Isn’t that my line?" you replied evading his question "Getting you to talk while I pour you some expensive drink and add to your tab?"  
"My night actually hasn't been bad so far" His voice was smooth he didn't even pause at your deflection only a small spark in his eyes let you see any change on his handsome face "Though I'd hear much rather about you."  
"I'm working" You could feel a small smile on your own lips. Although you saw the interest in his eyes he wasn't pushing or rudely hitting like other men did. The suit wasn't for nothing, this man actually had class.  
"I won't keep you" He tilted his head slightly to the right "But how about we mix business and pleasure?"  
"Oh working here already is a pleasure" you shot right back feeling brave and a little cheeky. True he did catch your interest but the night was young and who knew if he wouldn't move on to some easier target as he started to feel the effect of his expensive drink.  
"I'll get one question per drink I pay for?" His eyes met yours as he leaned forward just a bit. Never before had anyone proposed such a deal. It made this already very different man unique. You blamed that uniqueness for agreeing.  
"Alright" His eyes left yours wandering around the liquor shelf, studying all the labels intently he quickly found what he was looking for. With a small gesture of his head he pointed towards an almost new bottle on the upper shelf. "Some of that and your name, please"  
"(Y/n)" you said before turning to get the requested bottle. It was high enough that you had to stretch to reach it, your already short top rose up with the movement. Some whistles from the drunk group of men at one of the tables followed naturally, bur you ignored them. When you turned back to poor your most charming customer his drink you noticed his eyes on your face. He was looking at you, not your ass, briefly exposed back or tits when he again used that deep and fascinating voice to reply "I like that name, suits you"  
"Thank you"  
"So do you like it here darling?" he asked which caused you to frown a little.  
"Did you forget your own deal? It’s a question per drink"  
"Oh believe me no one knows deals better than me, darling. I'm in the business of making deals so to speak" He smiled and pointed you towards a younger man who was currently failing miserably at karaoke "Every drink I pay gets me one question. I'm paying for his drinks too"  
"Smart ass aren't you?"  
"Told you I have my experiences in the field"  
"Fine. Yes I like the work. It wasn't what I planned on doing with my life but here I am."

After a while he introduced himself as Crowley even apologized for being rude enough to not give his name sooner though you saw the smugness on his face too when you had to ask. Admittedly he made you curious. You were busy running around serving other customers but you felt yourself always drawn back to the place he was sitting. And with the amounts 'Dean', Crowley's bar buddy, was drinking he got a lot of questions to ask. They all seemed harmless enough, he never asked for any too private details. Some made you laugh like that time he wasted an opportunity to ask for anything instead he opted for the name of your first pet.  
As the night proceeded Crowley kept asking questions and you in turn tried to get to know him. It was rare that someone you met on the clock interested you enough for you to spend more than the polite five minutes of bar talk with them. Crowley was definitely something else.  
That's why you answered honestly when he asked when you would be getting off. It wasn't long anymore anyway. You hadn't realized how fast the night went by between work and talking to the suited man who ordered ridiculous girly drinks. Only twenty minutes left to be exact. For a second you felt a little sad about having your time with him end. But then again what did you expect? He was out with a friend who paid him little to no attention all he had been looking for was someone to talk to. As the bar tender you were the easiest option since you were sure to stay most of the night.  
"The night's coming to an end then" Crowley's eyes focused on you with an intense curiosity "May I ask you something?"  
"Haven't you all night?" A small smile played on your lips.  
"Let me take you home after your shift. I'm not ready to let the night end."   
You studied his face intently, usually you didn't let customers pick you up like that. It seemed unprofessional and cheap. If you wanted to meet someone you could do it in your own time. But this stranger interested you, something about him was different than all the other men who occasionally tried to pick you up. Maybe you could make an exception for him…  
"I…"  
Before you could say anything someone fell onto the stool next to Crowley. He wore a lazy smile while his eyes travelled down your body in a hungry way. You didn't like how his eyes on you felt, something about him seemed dangerous and it wasn't just his inappropriate wandering eyes.  
"I leave you alone with the pretty girl all night and you're both still here" the smirk in his voice was audible as his eyes once again travelled up your form to meet yours "Let's get out of here, sweetheart, before this guy bores you to death."  
You were kind of speechless by so much arrogance and cockiness. Who did this guy think he was?  
"Dean" there was a warning clearly audible in Crowley's voice. You didn't even need to see the warning shot his eyes gave the younger man. Was this really the man whose drinks Crowley had been paying all night? How did a man like Crowley associate himself with an asshole like Dean?!  
"What? The bet is still on and you had your shot" again a self-assured smirking tone in his voice "clearly the lady is not interested. Take a hint Crowley."  
"Bet?" You echoed looking back and forth between those very different men. You weren't sure what to make of this sudden development, but the uneasy feeling in your guts you had ever since Dean showed up only intensified.   
"Don't worry your pretty head about it, sweetheart" Deans hand was slowly making his way across the bar and you didn't dare take your eyes off it. But out if the corner of your eyes you still didn't miss the strain on Crowley's relaxed expression. What was the meaning of all this?  
"Crowley" your eyes still stared down Dean's curious hand "What bet?"  
"I… we..." The playfulness you had enjoyed so much when talking to Crowley earlier had vanished instead he sounded more serious.   
"We made a bet who could take the pretty bar tender home" Dean answered instead "And clearly this guy here isn't the one to show you a good time."  
"You bet… on me?" Suddenly you felt angry. This was exactly why you usually didn't let customers talk to you for too long. After all this was what most customers had in mind, chatting up the bar tender because apparently the usual drunk hook up wasn't challenging enough for some arrogant assholes who needed an ego boost.   
You felt foolish for assuming that Crowley was different from all the other men, just because he went about it in a more gentleman like fashion. Had you really been considering getting out with him? When had you become so easy? You should really work on your principles.  
"Darling…" Crowley's voice was still strained but you ignored it. You weren't some price to be won, so any of those two could boost their ego on a conquer.  
"To answer your earlier question" your eyes met Crowley's once more, though this time it was intense in a very different way "I'll be going home alone. Now excuse me gentleman, I'm still on the clock."  
You patted your own shoulder for how mature you had handled the situation, despite the hurt. Given their inappropriate behaviour and their treatment of you, you felt like snapping at them would have been highly justified. But you were a professional, unlike them.  
So after saying your piece you turned away to finished your shift. Your evening might have been ruined, but you still had about ten minutes of work left before your boss would start to clear out the bar.

You were drying up the last glass for the night when someone cleared their throat behind you. Reluctantly you turned around expecting your boss to tell you to hurry up. Instead it was Crowley again.  
"We're closed" you growled, no need for your polite work attitude anymore.  
"I'm aware" he replied "But I wanted to talk to you."  
"Dean was right you can't take a hint" you snapped putting down the dried beer glass forcefully "Let me spell it out for you again, very clear: I'm not interested. Now get out."  
"Quite interesting to meet the off the clock you." Crowley commented and ignored your demand to be left to your work "Feisty."  
"What do you want?"  
"I was actually trying to apologize for Dean's behaviour. You could say he hasn't been himself lately" a mysterious smile played up on the corner of his lips.  
"Fine. Whatever." Your tone suggested quite the contrary to your words. All you wanted was to finish up cleaning so your boss could lock up and you'd both could call it a night.  
"May I also add that his bet was entirely on him? He noticed my interest in you and I took him up on it to prevent him from picking you up just to get under my skin."  
"You need new friends."   
That made Crowley snort and you couldn't help a small smile spreading on your lips. Damn him and his way to charm you. Usually you never got attached to strangers so fast and easy. What was it with Crowley?  
"Are you offering?" His brown eyes softened as they met yours "I meant it when I offered to take you home."  
For a second you were torn. You hadn't been as intrigued with someone as you were with Crowley in a long time. But then again for all you knew he was still after winning his bet. Gentleman didn't exist anymore these days. No one was in for anything without the wish to gain something.  
"And I meant it when I declined" you let your eyes meet his one last time "It was nice talking to you though."  
"I enjoyed myself tonight and believe me, darling, I've seen more than you could imagine. If I'm intrigued by someone it means something." He sighed as he took his eyes of you and straightened his back "But I respect your wishes. It might even be for the best to not get close to me. I do indeed have a history of hurting the people I care too much about."  
"You're not a bad man. Make some different friends. It might change your history."   
Crowley nodded before turning to leave your bar. You looked after him as he walked out in his elegant suit. If you had met at a different time, under different circumstances you maybe could have been the friend he obviously needed. Maybe something more. But with the way things happened it wouldn't have worked out. Sometimes some stories simply don’t get the chance to play out.  
Though ever since that night a part of you would always wondered what could have happened. You would never know for sure, but you could still dream about the untold story of you and the handsome stranger with the intriguing eyes.


End file.
